Azo-dyestuffs from 2-3-hydroxynaphthoic acid arylides and process of making the same



Patented July 24,1928.

LEOIPOLD LASKA AND ARTHUR- ZITSCHEB,

ASSIGIFI'ORS TO GRAS SELLI DYESTUFF CORPORATION, OF NEW YORK, N. Y., ACOR-' PORATION OF DELAWARE.

OF OFFEN'BACH-ON-THE MAIN, GERMANY,

AZO- IDYESTUIEFS FROM 2-3-HYDROXYNAPHTHOIC ACID ARYL IDES AN]? PROOES OFMAKING THE SAME.

i No Drawing.

The present invention relates to new azo dyestuffs from2-3-hydroxy-naphthoic acid arylides and a process of preparing the same.

,We have found that valuable novel azo dyestuffs are obtained if2.3-hydroxynaphthoic acid arylides are allowed to couple with the diazocompounds obtained from amines of the general type:

wherein R and R, represent an alkylor an aryl group and X an alkylfor analkoxy group. g

The-most probable graphical representation for our novel dyestuffs isthe formula:

as such or on a base, i.,e., on a substratum or on the vegetable fiber.When mixed with or precipitated on substrates these novel dyestuffsproduce valuable color lakes. They are'furthermoreof great interest inthe dyeing of vegetable fibres. The dyestufi 5 is in this case directlyproduced on the fibre, the dyeings obtained are of exceedingly clearshades and particularly fast to kier boiling.

The amines of the aforesaid type may be prepared by 'oausingarylsulfonicacid chlorides further substituted besides by a nitrogroup in thebeforedescribed manner to react on primary or secondary amines, whichApplication filed May 24,1928, Serial No. 111,371, and in Germany m 28,1925.

may, so far as they belong to the aromatic series, contain furthersubstituents in the aryl residue, and by reducing the nitrocompoundsthus obtained.

The, following examples will further illustrateour novel process and theproducts obtained by it. We wish it however to be un-' derstood that weare not limited to the particular conditions nor to the specificproducts mentioned therein. The parts are by weight.

' Example 1. p

13.8 parts of 2-amino-toluene-et-sulfoN- methylanilide are thoroughlystirred up with 23.2 parts of hydrochloric acid .(spec.

gra-v. 1.160), 75 parts of water and ice are added, and then diazotizedwith a solution of 3.5 parts of sodium nitrite in 15- parts of Water. Tothis solution a solution of 16.5 parts of2.3-hydroxynaphthoyl-a-naphthyL amine in 14 parts of caustic soda (36136.), 1 part of Turkey-red oil, 6 parts of crystal sodium acetate isrun in. The coupling is finished after several hours stirring. Thedyestuif is thus obtained in the form of a brilliant red paste. Whenmixed with the usual substrates it forms valuable bluish red lakes.After drying it dissolves in concentrated sulfuric acid with a bluishwine red color and has mostprobably the formula:

Well boiled out and dried yarn is impregnated with a solution containingper liter 10 gr. of 2.3-hydroxy-naphthoyl-4- phenetidine, 15 'cc. ofcaustic soda (34 B.) and 8 cc. of Turkey red oil. It is then well wrungand without drying developed with a solution, containing per liter thediazo compoundof 5.5 gr. of Q-amino-toluenei-sulforN-methylanilid whichhas been neutralized with sodium acetate. After rinsing, soapmostprobably the formula:

-The same shades and fastness properties are obtained by producing thedyestufi's' on the fibre by the usual printing processes.

The following table gives the shades obtained on cot-ton material byusing other of our novel azo combinations Combined with Diazocompoundof: 2.3-hydroxynaph Shades:

thoyl:

2-arnino-toIuene-4-suliodimethylamid of the formula:

4 chloro 2 anisi- Clear yellowish dine. red. 2-phenetidine Clear orangered. a-naphthylamine" Clear red. fl-naphthylamine. Fiery scarlet.

2 amino 1 ethoxyphenyl 4; sulfodirnethylamid of the formula:

N H: cano-Oso, 4 chloro-2-anisi- Bluish red.

N(CH:)2 Do a-naphthylamine- Bluish red. Do B-naphthylamine. Bluish red.

' j 2 amino toluene 4 sulfo- N methylanilid of the formula:

CH 1 3-toluidine. Fiery scarlet.

0 H, Fiery scarlet. Do 4-chioroaniline Clear red. De 5 chloro-Z toluime.Do 5; chloro 2 anis- Fiery scarlet.

ldllle.

lVe claim:

1. In processes of producing azo dyestuffs from 2.3-hydr0xynaphthoicacid arylides the steps comprising diazotizing an amine of the generaltype: a

R so, -N

wherein R and R represent an alkylor an aryl group and X- an alyklor analkoxy.

group, which dyestuffs are in the dry state reddish to dark coloredpowders, soluble in concentrated sulfuric acid with from blue to darkviolet colors and which by reduction yield an amine of the type:

R SOINJ HIN Rl wherein R and B represent an alkylor an aryl group and Xan alkylor an alkoxy group, and al-amino-2-hydroxynaphthalene-3-carboxylic acid arylide, and which whenproduced on vegetable fibers produce reddish shades of an excellentfastness to kier boiling.

3. Vegetable fibres dyed with the dyestufis of claim 2.

In testimony whereof, we aflix our signatures.

LEOPOLD LASKA. ARTHUR ZITSCHER.

